


Bart's Lesson

by YoshisGallery



Category: The Simpsons
Genre: Gay, M/M, Masturbation, Underage Masturbation
Language: English
Status: Completed
Published: 2020-08-12
Updated: 2020-08-12
Packaged: 2021-03-05 23:14:18
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 4,140
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25853455
Author URL: https://archiveofourown.org/users/YoshisGallery/pseuds/YoshisGallery
Summary: Bart Simpson gets a valuable life lesson from his beloved older friend Roy.
Relationships: Bart Simpson & Roy
Kudos: 25





	Bart's Lesson

“Hey, dude.”

Roy glanced up from the TV as Bart came in through the front door. 

“Roy! I didn’t know you were here!” Bart said, his previously world-weary face lighting up like a neon sign at the sight of his older buddy. Not technically related to him as far as Bart knew, Roy was an occasional house guest of the Simpson family who came and went with little notice. Bart never really knew exactly who Roy was and why his parents were so accommodating of the 19 year old, but he never really cared. Roy was the coolest guy Bart knew, and treated him like a true friend. 

“Yep, I’m in town for the weekend, bro.”

“Awesome!” Bart dumped his backpack on the floor by the door and ran over to him. Roy stood up from the couch and swept up the younger boy in a big bear hug, before plopping them both down on the couch.

“How’s school going, dude?” Roy said as Bart practically embedded himself into Roy’s left side.

“Eh. It sucks,” Bart responded, crinkling his nose with distaste. “Same boring old crap.”

“Yeah, I hear that. School sucks,” Roy agreed.

“Yeah. And the guys at school are jerks,” Bart pouted, his dour expression returning to his face. Obviously something fresh was bothering him.

“Oh? What happened?”

Bart looked away uncomfortably. “Eh. Some of the older guys were calling me a baby.”

Roy cocked an eyebrow. “What? Well, screw them. You’re already becoming a man.”

Bart fidgeted and didn’t respond. Roy mentally shrugged to himself and let the subject drop. The two of them watched TV for a little while in silence, until Roy’s phone chimed an alert. He picked it up off the side table next to him and read the text message.

“It’s your mom… looks like your folks are gonna be out for a while. Your sister’s got her music recital.”

“Ugh, fuck that,” Bart said with feigned casualness. 

Roy cocked an eyebrow. “Whoa, dude, when’d you learn to talk like that?”

Bart looked a bit embarrassed but tried to shrug it off. “Isn’t… that how guys talk?”

“Yeah, I guess… usually if you’re a bit older.”

Bart’s face became redder and contorted into a pained scowl. “You said I was becoming a man!”

Roy rolled his eyes and sighed. “Yeah, I guess I did. Okay… as long as you don’t tell your folks, I don’t care.”

Bart’s face changed as quickly into a big delighted grin as it had into the scowl before. “Fuck yeah!”

Roy laughed despite himself. It was only a few months prior that Bart was still acting like a little boy, and now all of a sudden he was doing his best to be a grown up, despite the fact that he was back to cuddling up against Roy’s side like a child. “Yeah, dude, fuck yeah!” Roy agreed.

Bart beamed. Roy really was the greatest guy he knew.

“So whatcha wanna do? It’s just you and me this afternoon.”

“Uhh… I dunno. I got a new video game that’s pretty sweet.”

“Oh yeah? Let’s see it!”

Bart bounced up from the couch and went over to the TV, pulling a video game console out from the cabinet. He fired the game up and babbled excitedly about the game and how it worked. Roy was already familiar with it, but he let Bart rattle off joyfully for a while. After about 20 minutes of watching Bart bumble his way through some fairly easy levels, however, Roy was starting to get a little bored. “Hey, mind if I give it a shot?”

Bart was silent for a bit as he hobbled his way through the game, but then eventually said, “Yeah, sure.”

He turned the controller over to Roy at the next break in the game. Roy quickly began blasting through the level with a much more honed skill than Bart, and Bart quickly realized Roy already knew the game better than he did. “Hey! You already know this!” 

“Yeah, dude, but I liked how you explained it. You got a sharp eye.”

Bart’s incredulous expression vanished at the compliment, and he quickly got focused on watching Roy plow through the game, showing Bart all sorts of new tricks he never knew before.

“Shit, dude, you rule!” Bart cheered as Roy made easy work of one of the big bosses that Bart never could pass.

“Heh. Gotta ask, dude, are you cussing cuz of what those guys said to you?”

Bart went silent for a bit and started looking away again. 

“Man, fuck those guys, I told you,” Roy assured him.

Bart opened his mouth as if to say something, then closed it again. His face became twisted with frustration.

“Bro, what is it? You know you can tell me shit.”

Roy’s casual swearing seemed to soften Bart’s demeanor. Exhaling quickly in frustration, he turned back to face Roy. “One of them said something about ‘jerking off’ and I didn’t know what it meant. Then he told me if I didn’t jerk off I must still be a baby. And then they all laughed at me.” His face was flushed again.

Roy shifted a bit uncomfortably. He wasn’t expecting something quite so… blunt. After a moment of hesitation, he responded, “Oh, well, that doesn’t mean anything, man.”

Bart gave him a look of suspicious disbelief. “You’re fulla shit.”

Roy looked guilty. The ruse hadn’t worked. Maybe he shouldn’t be trying to deceive him, especially since he HAD told Bart that he could tell him anything.

“Well, it’s… something you do when you start getting older.”

Bart’s eyes bore determinedly into Roy’s.

“Well, you know… uh…” Roy chewed his lip. He guessed Bart is gonna find out sooner or later, and it might as well be from him. “You know, when your dick gets hard?”

Bart’s face immediately flushed red again and his gaze faltered a bit. A bit shakily he responded, “Uh… yeah.”

Roy tilted his head back and forth a bit. “Well… that’s called getting horny.”

“… Oh. I’ve heard of THAT.”

“Yeah, well, when you get horny and your dick gets all hard, you… uh, you jerk it off.”

Bart looked a bit perplexed. “Uh… what’s that?”

“Ya know… you grab it and… stroke it for a while.”

“Oh. …. Why?”

Roy squirmed a little more. This was incredibly uncomfortable. And this talk of jerking off was starting to make his own dick swell a bit by its own will. As casually as he could, he adjusted his seated position on the floor so that his large dick would point down the leg of his shorts instead of up towards his hip bone.

“Cuz it feels good. It… gets rid of the horniness.”

Bart’s eyes were wide as saucers. “Really?”

“Yeah. All guys do it.”

Bart tilted his head a bit. “Oh.”

Sensing Bart’s curiosity was finally sated a bit, Roy shifted his attention as noticeably as he could back towards the video game and started playing it again.

Then, after a few minutes, Bart spoke up again. “How… how does it work?”

Roy felt his face start to burn. So much for dodging the subject. He paused the game again, figuring he wasn’t going to get out of giving his young buddy the full story.

“Well, when you get hard, you… grab your dick… and stroke it up and down for a while.”

“Yeah, but what’s that do?”

“It, uh… it makes you cum.”

“Come…?”

“You know… you have an orgasm.”

“Ohhh. We learned about that this year in sex ed!” Bart finally felt like he was no longer totally in the dark, and was obviously a bit relieved. “But… they said it happens when you have sex.”

Roy shrugged awkwardly. “Yeah, it happens then too, but… you can do it yourself.”

Bart looked upwards quizzically. “Oh.”

Roy started playing again, but after only a minute, Bart spoke up again. “How?”

Roy sighed. “I just told ya, bro.”

Bart hemmed a bit, but then said, “Yeah, but I don’t really… get it.”

Roy paused the game yet again. “When you get horny, you’ll understand, man.”

“… But I get horny all the time.”

Roy chewed his lip again. His own dick was starting to respond again to all this talk about jerking off, and he fidgeted again. “Well, maybe you should try it sometime, dude.”

Bart looked away in thought for a bit, then, sheepishly, “When do I do it?”

Pausing yet again, Roy responded with restrained exasperation, “When you get horny, man, I told you!”

“I’m horny NOW.”

Roy’s eyes bugged out a bit in shock. Bart slowly and meekly pointed toward the crotch of his shorts, which were tenting noticeably.

“Oh.” Roy chewed even harder. His own dick was starting to swell up alarmingly in his shorts now.

“Well, uh… you could… uh…”

Looking both embarrassed and curious, Bart went past the point where he otherwise would have stopped with anyone else he knew, even his best friend, Milhouse. “Could you, ya know, maybe… could you teach me? I really don’t know how to do it.”

Roy tried not to groan. How could he get out of this? SHOULD he try to get out of this? Bart trusted him so much, and he really loved how much Bart looked up to him. Telling him no could send a really bad signal, and might even damage their close relationship.

“Uh… yeah, I guess,” Roy managed to squeak out.

“Um, cool…” Bart looked relieved that Roy hadn’t embarrassed him during such a vulnerable moment. “Ya know… it looks like you’re… horny too, ya know.” Bart was looking down at Roy’s shorts with a contorted smile. Despite being angled along his leg, Roy’s now full erection was still very obvious.

“Yeah, well… I do get horny a lot, dude.”

“Do you… do you jerk off a lot?”

“Yeah,” Roy admitted. He decided the best tack right now was to be as honest with Bart as he could be, and to tell the truth, he really was horny as hell. He had just gotten into town after a couple day’s travel and hadn’t really had much time to himself… usually he’d jerk off once a day at least to keep his hormones at bay. “Usually every day.”

“Really? Wow…” Bart said with awe in his eyes.

“Yep. It’s totally normal for dudes.”

“Cool…” 

Bart sat silently. The 800 pound gorilla in the room wasn’t just going to go away.

“Okay, so… uh…” Bart verbally nudged.

“Yeah, uh, so… let’s go to your room.”

Bart smiled quite nervously and stood up gingerly. His shorts were still bulging outward. He’d obviously been growing up faster than Roy had realized. “Okay.”

After one last moment of hesitation, Roy stood up to follow Bart upstairs. Bart stared for a brief moment at the huge swelling in Roy’s shorts that the teenager was no longer trying to hide, but then quickly gained his composure and scrambled up the stairs. Roy felt a bit manipulated as he followed the boy, wondering if this was some kind of trick. He knew Bart well enough to know that it wasn’t, but… he definitely had a way with persuasion at least. It was almost as if Bart had calculated exactly how to steer that conversation ahead of time. “Eh… nah,” Roy decided to himself.

He walked into Bart’s room, and closed the door behind him. No more chance to escape from this, so he might as well do it as casually and coolly as he could, to show Bart that it really was no big deal. But he realized right then that he did have to make sure this didn’t come back to him. He knew that if anyone found out, it could go really badly. Bart WAS still a boy. It was all his idea, but… no one else would believe it. 

“So, dude… you need to promise me you’re not gonna tell anyone I’m showing you this, okay?”

“Oh… yeah, ‘course.”

“I mean it, bro, this is just you and me. Okay?”

“Uh, yeah. Totally,” Bart said as if it was already understood. Well, he figured he might have bragged to Milhouse at some point, but Roy seemed pretty serious about it. “I promise.”

“Okay, cool, man… you know I trust you.”

Bart smiled at the compliment. Roy really was the best.

“Okay, dude… you can take your clothes off.”

“Uh… oh, okay,” Bart said, blushing a bit. He quickly did as he was told, though, shucking his shirt and then his shorts onto his bedroom floor. 

“Get on the bed, it’s more comfortable that way.”

Bart climbed up onto the bed and lied back against the pillow, his dick at full mast within his white briefs.

Gathering up his last bit of courage, Roy unbuttoned his shorts, and pulled them down. He then pulled down his boxers, letting his dick spring forth for Bart’s full viewing.

“Wow…” Bart said with unrestrained awe. Roy’s dick was at about 75% erect at the moment, but even at that state was a sight to behold. He was well above average in size, and rather proud of it. Bart’s staring only made him stiffen up even more.

“Scoot over a bit, dude.” Bart slid a bit to his left, getting close to the left edge of his small bed. Kicking the shorts and underwear free from his feet, Roy plopped down beside him, barely fitting onto the mattress. Lying back, he let his dick stand straight up and proud so Bart could ogle it as intently as he desired. He unbuttoned his shirt all the way down and pushed the two halves aside, exposing his whole body to his young friend. All hesitation was gone at this point… he was feeling way too proud of himself at this point, and was eager to begin Bart’s lesson.

“Your dick is huuuuge,” Bart said, his eyes nearly popping from his skull.

“Well, let’s see yours too… ditch the underwear, bro.”

Bart broke off his stare, then glanced down at his own swelling member. Sensing his hesitation, Roy said, “It’s totally cool, dude, I can already tell you’re pretty big. I wanna see it.”

That was the right amount of encouragement that Bart needed to proceed, so he put his thumbs under the waistband of the briefs and pulled them down. His fully swollen dick sprang back from its cotton confines and loudly slapped against his belly as he pulled them off his legs and kicked them down to the floor with the rest of his clothes.

Now with the two of them totally exposed to each other, they sat silent for a while, just gazing at each other’s bodies. Bart was making no attempt whatsoever to hide his fascination with Roy’s huge dick and toned, slender adult body… his gaze running from the fat, bulging sac at the base of Roy’s dick, up to the neatly trimmed patch of hair around the top of the base, then up his firm belly and finally up to his reasonably well-defined pecs and large, plump nipples.

“You are pretty big, you know…” Roy said, nodding appreciatively at the swollen cock Bart was holding around the base with his left thumb and forefinger. Roy wasn’t really all that interested in guys, though he was no stranger to jerking off with buddies and several instances of experimentation beyond that, yet his complimenting of Bart’s dick was sincere. Even though the boy was barely into puberty, his dick was already showing signs of the man he would become… rather than the thin, featureless cylindrical shaft of a little boy, Bart’s dick was already decently long and had the pronounced bulge running along the bottom that was a sure sign of progressing manhood. 

“Heh… thanks,” Bart grinned impishly.

After those several minutes of soaking in the sight of each other’s naked, fully aroused bodies, Roy finally said, “Alright, dude. Time to learn how to jerk off.”

“Alright, cool,” Bart said, trying and failing to sound casual. He stared intently as Roy’s right hand wrapped around his own cock about halfway up his long, firm shaft, then followed suit with his left hand around his own smaller but still rigidly hard one.

Roy was so hard at this point that it was almost painful to touch his dick. The sexual excitement and taboo nature of what he was doing with his young friend had him already quite built up and he didn’t want to end things too quickly, so he proceeded slowly and gently.

“Okay dude, just do what I’m doing. Don’t grip too hard.” 

Bart had obviously been gripping his dick tightly, unfamiliar with the nuances of the act. Obediently he loosened up a bit.

“There ya go, that’s it. Okay, now follow me.” Roy began to slowly stroke his cock, up to the base of his glans and down almost all the way to his crotch, about one pump every two seconds.

Bart followed Roy’s motions in perfect rhythm, stroking his own rock-hard dick for the first time in earnest. A weird little sensation started tickling the back of his mind, something unfamiliar and kind of confusing.

“How’s that feel, bro?” Roy inquired, continuing with the slow, deliberate strokes. He was almost a bit jealous, knowing that Bart was feeling such a wonderful thing for the first time.

“It… it’s kinda weird.”

“Give it time, dude. It takes a little while to build up, but it starts feeling better and better.”

Bart nodded, alternating his view from Roy’s hand stroking his huge dick to his own hand stroking his smaller one. Even though Roy was a lot bigger than him, any lingering sense of shame that he might have felt before was dispelled by Roy complimenting his size. He was starting to feel good now, as Roy had promised.

Almost subconsciously, Bart scooted his butt over a little to the right to be up against Roy’s left side. Their bodies were now in contact from Bart’s shoulder all the way to his knee. Roy’s warmth and closeness was extraordinarily pleasant, and the skin-on-skin contact was making him tingle all over.

Bart’s movement to be closer to him made Roy’s head swim a bit. This was becoming a lot more exciting than he would have ever guessed. He didn’t want to do anything that might even conceivably scare Bart, but he too wanted to be a little closer to his new jerking buddy. So he casually lifted his left arm and draped it around Bart’s left shoulder. Bart gave no sign of discomfort, and in fact started to grin even more at the intimate gesture.

“How’s it feeling, dude?” 

Bart’s eyes started to glaze over a bit. It was pretty obvious that he was really starting to understand the enjoyment of what Roy was teaching him. “It’s good… that weird feeling is getting stronger.”

“That’s good, that’s what’s supposed to happen.”

Roy couldn’t stand the slow pace any longer, so he started to gradually increase the speed of his strokes. Bart mimicked the new pace, still glancing from his own dick to Roy’s, though as his gaze became more heavily lidded, he was spending more time watching Roy. 

“Dude… are you peeing?” Bart suddenly said, as he suddenly noticed that there was a clear liquid oozing out from the tip of Roy’s reddening cock.

“Heh… nah, dude. That’s precum. When you’re really horny you start to leak it.”

Bart watched in awe as the mysterious new fluid started to spread out along Roy’s glans. “Wow…” 

As his pace continued to gradually speed up, more of the liquid came out, now slickening much of the upper part. “Yeah, it’s good. It means I’m getting close to cumming.”

“Oh…”

Now fully absorbed by the sensations, Roy’s left arm tightened a bit more around Bart’s shoulders, and Bart pressed even closer up against Roy’s body. The younger boy was no longer trying so hard to mimic Roy, now that he’d found his own rhythm and was earnestly masturbating for the first time. 

It felt good. So very, very good. Why had he not done this before? He wasn’t sure he ever wanted to stop. And Roy felt so good against him. His strong arm around his shoulders. So incredibly good. And something about Roy’s smell. Something was different. Comforting. Fascinating. Man, Roy smelled so good. How did he smell so good? So good… 

Then the sensation began to change. “Roy… Roy, I feel a little funny…”

“Shh, dude, just keep going. Trust me.”

“Ah… okay… ah…” Bart’s head started to feel really strange, and some kind of foreign-feeling energy was running up and down his whole body. He wanted to stop, afraid of whatever this kind of scary new thing was, but Roy was watching and he didn’t want to disappoint him. 

Then he felt like he was suddenly about to pee all over himself. “Ah… Roy… I think I’m gonna…”

Then, as he somehow lost all control over his body and his head threw itself back into the pillow, some kind of amazing, violent, absolutely indescribable feeling exploded through his body as his cock throbbed and pulsed in ecstasy. Gasping raggedly, his hand continued to stroke his dick by its own will as the beautiful, bizarre sensation nearly tore him apart.

Then, soon, it rapidly ebbed away, and his consciousness started to come back. Breathing heavily to try and catch his breath, he opened his eyes, slowly focused, then turned to Roy.

Roy was grinning hugely at Bart, his eyes full of delight. “Awesome, Bart. Really fucking awesome.”

Bart stared bewildered for a moment at Roy, then his mouth burst into a gigantic smile. “Ho… holy shit, man… holy shit. Holy…. Holy shit.”

Roy chuckled. “Look, dude, you came.”

Roy’s hand was no longer gripping his dick, instead pointing down at Bart’s belly. There was a small, slightly cloudy streak of viscous liquid running from his lower chest to just under the head of his cock.

“Wow…”

“Yeah, see? I told ya you’re becoming a man. Little boys don’t cum.”

Bart grinned ear to ear. He was delighted beyond words that he actually came, and that Roy seemed so proud of him. And boy, did he feel good. Sooooo good all over. It was like his ears ringing after a really loud noise, except all over his body.

“Wanna see me cum now?” Roy said, returning his hand back to its grip on his red, precum-slicked cock.

“Yeah!”

“Okay, cool… don’t be surprised, it’s gonna be a lot.”

“Oh… okay…” Bart’s attention was no longer on himself. He was now 100% fixated on Roy. 

Encouraged by Bart’s fierce interest and eager to get back to his own pleasure, Roy finally let himself go full-speed ahead. Alternating his attention between his own dick, Bart’s naked, cum-dribbled body, and his own pre-orgasmic delirium, it took less than a minute to hit the point of no return. 

“Ahhh…. Ahh— Bart… watch… I’m gonna cum….” Roy said breathlessly, then screwed his eyes shut as the orgasm overtook him.

Bart stared with unblinking fascination as Roy’s cock erupted with semen. Huge, thick, pearly white strands of the stuff shot out, one after another after another, streaking Roy’s torso with the gooey stuff as he grunted and gasped in the throes of helpless passion. After about a minute, with the orgasmic pulses receding away like the tide, Roy finally opened his eyes.

Bart looked like his eyes were going to fall out. His mouth hung open in sheer amazement, with only the upturned corners showing it was a look of delight.

“That was FUCKING AWESOME!!” Bart said, nearly shrieking. “Holy SHIT! Look at all that cum!”

Roy smiled drowsily. “Told ya it was gonna be a lot.”

“Is it always that much?!”

“Not always… but if you don’t do it every day, it does build up.”

“Wow…” Bart continued to stare at the thick ropes of semen all over Roy’s body. Without asking, he reached his left hand over across his body and put his finger into one of the puddles. “Oooh… it’s really thick!”

Roy was still in full afterglow, so he just smiled and let Bart poke at his cum. He swirled it around on Roy’s abs for a little bit before his curiosity seemed satisfied. Cuddled together on the bed, the two lied motionless for a while, basking in each other’s enjoyment. Roy never would have guessed this would happen… hell, he never even thought about it before. But now he was really glad.

Bart pressed his cheek against Roy’s left pectoral. He could hear Roy’s heart beating, rapidly but gradually slowing. He’d never guessed anything so great was even possible.

“Roy?” he said after a long while.

“Yeah, bro?”

“When can we do this again?”


End file.
